Terrible Twos: Dispelling Common Entrepreneurial Myths and Folktales

When you leave the corporate grind for the loose, unstructured entrepreneurial life, you leave behind the need to show up anywhere in person, report to anyone, get dressed for the day, or plan for vacations—because every day is a vacation.

Said no self-employed business owner clearing year two, ever.

In actuality, I and other entrepreneurs with which I have discussed this topic often find the opposite to be true: you trade that trusty biweekly paycheck for feast-or-famine roulette pay cycles, increased tax burden, undesirable fusion of work and personal life, ‘daycations’ at best, strengthened biases and echo-chamber thinking due to lack of human interaction, an office or working space that functions as a literal echo-chamber due to lack of human interaction…and the list goes on.

Yet, most of us who are still doing this terrifying solo thing absolutely love it, each of us for similar or completely dissimilar reasons. 

Regardless of the reasons, the myths of entrepreneurship live on, even multiply. In this blog post, I’ll attempt to address and hopefully dispel some of the more troubling ones I’ve come across in my experience as a full-time self-employed professional and business owner (or, “CEO, CTO, COO, Founder, Owner, and Visionary of a multi-disciplinary single-member LLC with 10+ years’ proven track record providing research-based creative marketing content for small- and medium-sized businesses and startups” for those of you with LinkedIn-for-brains).

#1: Corporate America is exploiting you. Start your own business and gain complete control of your professional and personal life.

LinkedIn serves me up some terrible things. Algorithmically, that’s my fault (or so we’re told), but one of the worst of them showed up in a post by a self-proclaimed “loud-leaver” written in provocative, double-spaced influencer fashion about evil corporate America and all the ways they’re just dying to lay you off. He’s some sort of doctor, according to his LinkedIn, so we’ll call him Doc. Not only does Doc obviously not understand at-will employment, he makes the fundamental mistake of promoting entrepreneurship as a panacea against all of the alleged evils of big business.

Doc rants furiously about the injustices of being laid off by companies “because they [can].” At face-value, this does seem like a really crappy thing: big businesses sucking the life force out of its drones, then spitting out their shriveled carcasses like walnut shells. However, when you consider that irksome thing called at-will employment, it becomes apparent that this is not only normal, it’s legal (unless some form of discrimination or other illegal reason is a factor in an employee's termination). Further, this is exactly the same power Doc is exercising in loud-leaving. It works both ways—always has, probably always will.

What’s more damaging than Doc’s misunderstanding of at-will employment, however, is his misconstruction of the entrepreneurial path. He spends about 90% of his snarky post raging against evil corporate America, and 10% (two sentences) urging people to build something to generate their own income streams. Two sentences. It’s just that simple: leave your job and just start making money. Why didn’t we think of that?

Most people don’t jump off the cruise ship into shark-infested waters to escape the tyrannical crew members.

Most people (unlike Doc) don’t jump off the cruise ship into shark-infested waters to escape the tyrannical crew members. My own business started over ten years ago and grew slowly as I worked my full-time job. It wasn’t until the fall of 2023 that I felt I was ready to jump, but I made that jump only because I had shark repellent and a life jacket—and the parts and experience required to build my own boat. No one should ever just jump, and especially not because they “might possibly be facing a layoff.” That’s perhaps motivation at best if you’ve already got a solid foundation and years of growth under your belt, but only then.

Last but not least in all of this: why are we treating corporate America with such a deep level of contempt? Who are we selling to now anyway, as entrepreneurs? Other entrepreneurs only? Does Doc not want any business here in corporate America? Is he doing business overseas? Does that complicate his tax situation? Lots of questions, and a convenient lack of answers.

In sum, this sort of thinking is not only short-sighted, it’s damaging to budding and burgeoning entrepreneurs. Building and running a business is one of the hardest things in the world to do; let's give it the respect and forethought it rightly deserves. Also, I’d encourage those with an entrepreneurial bent to think in terms of building a “business.” “Income streams” brings to mind YouTubers and OF stars. You can potentially sell a business or pass it on to posterity; you probably would have a hard time doing the same with a YouTube channel or a similar "income stream."

#2: Entrepreneurs can be productive anywhere, anytime. The 8-5 grind is for corporate losers only.

I spent fifteen-plus years working a dressed-up, eight-o’clock-is-late corporate job—first as a help desk technician and systems administrator, then as a marketing and design manager. This was the COVID antebellum era—none of this postbellum hippie garbage like “work-from-home” or “hybrid schedules” was even conceivable at that time, and it’s such a shame. There are a plethora of studies available that provide evidence for large leaps in productivity since flexible schedules and work-from-home options were introduced, but I will argue only from my own experience as a designer and knowledge worker in general: my productivity has skyrocketed since I started working remotely some five years ago.

There isn’t just one reason for this. To say that COVID created opportunities like these for people is a bit morbid. People suffered in so many ways during shelter-in-place—physically, financially, mentally, you name it. When considering a somewhat abstract concept such as productivity, it must be defined by person, skillset, industry, and a whole slew of other factors. I won’t do that here, but I will say that what working remotely—and, more specifically, becoming self-employed—has afforded me is the ability to create my own ideals around productivity, and then map and chart them from there.

I started out my first year as a full-time entrepreneur doing what most of those who jump off the boat do: I mimicked. I just did what I used to do for the people I used to work for, and structured my day the same way I did when I was doing that sort of thing. It stopped working pretty quickly. It wasn’t until earlier this year that I finally realized I needed to structure my day during my peak performance periods—from around 9am-3pm—in order not only to maximize what I’m calling my productivity, but also my enjoyment of the work I’m doing. A running theme over the course of my days in the office was a noted lack of enjoyment, and that’s because we all work in unique ways and in very different skillsets, one to another.

So yes, while entrepreneurship does afford me the ability to set my own schedule (see my post on the 90-90-30-30), and no, I’m not usually grinding it out anymore, by no means does a self-employed lifestyle lack structure (it shouldn’t if you’re doing it right). I would say I’ve become lots of percents more structured (and more mathematical, in turn) since leaving managed job roles at other companies. I’ve had to become the manager, the technician/skilled laborer, and the visionary. And the bookkeeper. And tax specialist. And payroll admin.

Also, since I operate on an elaborate system of 4+ monitors and macropads, I’m still chained to my desk when I’m doing any of the real (i.e., billable) work. I’m not on some beach in Cabo, I assure you.

#3: Bring on that unlimited vacation time.

Ah, the life of a rich entrepreneur. Let me tell you about some of the people I know.

One of my friends and clients went out on his own a month before I did back in 2023. He needed websites, videos, logos, the works. As we worked together on building his brand, I learned a lot about him. I learned that he was definitely making money, but he was investing it back into his business. While I made it a point to always make sure I was paying myself a salary, I could easily admire his reasoning in that. He was giving things away for free (I’ve done it a lot too—and I mean beyond what I would actually consider pro bono work); he was speaking, consulting, winning, losing.

When he finally took his first vacation, it was a retreat so he could get into a different mindset. Just so he could get out of his modus operandi.

Another friend, client, and entrepreneur owns his own shop and can be found most days sitting at one of the tables in his establishment working, focusing, maintaining. 

These guys aren’t vacationing at the Aix-en-Provence; they aren’t sitting back and letting their “income streams” magically produce gold nuggets. If anything, this should be a scolding reminder to both of them!

There is no shame in going on vacation. We should be taking them more frequently. My only point in saying any of this is to dispel the myth that being self-employed means you get to up and vanish off to the Moors like a friggin’ fart in the wind whenever you feel like it. It’s just not so. As I said, we’re all we’ve got: we’re the manager, the technician, the PR person. We’re HR and A/P. If anything, we’ve got to plan and save more than a salaried employee to afford the time off to go to Legoland.

To conclude this post that could only be considered Proustian in length, entrepreneurship is a wonderful and rewarding lifestyle. You and your clients impact one another in amazing ways that you can’t experience at a desk job; people are usually willing to pay your premium rates in return for your expert work; you learn and grow exponentially in so many areas throughout your entrepreneurial career; and eventually, you get to pass the baton to kin or even sell your business. It’s a bit like owning vs. leasing a home, except with your job—and much like owning vs. leasing a home, car, or some other asset, there isn’t always a black-and-white “right or wrong” reason to do one over the other, despite what Doc would have you believe. Just because there’s a mutiny on deck doesn’t mean those sharks aren’t ready to eat you alive, piece by piece.

Don’t be fooled. Don’t be hasty. But, for the love of Mike, don’t be afraid to start (small).

You can find other helpful posts about my entrepreneurial journey by browsing my blog at www.kanyondesigns.com/blog.